2-[(E)-(4-Fluoro-benzyl-imino)-meth-yl]-4-methyl-phenol.

In the title Schiff base compound, C(15)H(14)FNO, the benzene rings make a dihedral angle of 72.75 (13)°. The mol-ecular structure is stabilized by an intra-molecular O-H⋯N hydrogen bond. In the crystal, weak π-π stacking occurs between the phenol rings of inversion-related mol-ecules, the centroid-centroid distance being 3.7731 (14) Å.

Related literature

For background and related compounds, see: Cohen et al. (1964 ▶); Xia et al. (2009 ▶).

Experimental

Crystal data

C15H14FNO

M = 243.28

Monoclinic,

a = 15.0297 (9) Å

b = 6.1496 (3) Å

c = 14.3090 (9) Å

β = 104.142 (6)°

V = 1282.45 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.38 × 0.21 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

9046 measured reflections

2265 independent reflections

1552 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.150

S = 1.10

2265 reflections

164 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027018/xu5548sup1.cif

Structure factors: contains datablock(s) 1. DOI: 10.1107/S1600536812027018/xu5548Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027018/xu5548Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H14FNO	F(000) = 512.0
Mr = 243.28	Dx = 1.260 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2338 reflections
a = 15.0297 (9) Å	θ = 1.0–25.0°
b = 6.1496 (3) Å	µ = 0.09 mm−1
c = 14.3090 (9) Å	T = 293 K
β = 104.142 (6)°	Block, yellow
V = 1282.45 (13) Å3	0.38 × 0.21 × 0.14 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	1552 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 25.0°, θmin = 2.8°
ω scans	h = −17→17
9046 measured reflections	k = −7→7
2265 independent reflections	l = −16→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0477P)2 + 0.4777P] where P = (Fo2 + 2Fc2)/3
2265 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.02053 (15)	0.5287 (4)	0.65069 (15)	0.0460 (6)
O1	0.10373 (12)	0.2040 (3)	0.63178 (13)	0.0702 (5)
H1	0.1454	0.2793	0.6633	0.105*
C7	0.10205 (17)	0.6427 (4)	0.70213 (16)	0.0553 (6)
H7A	0.0966	0.7852	0.7218	0.066*
C6	0.02389 (17)	0.3154 (4)	0.61582 (16)	0.0515 (6)
C5	−0.05629 (19)	0.2196 (4)	0.56346 (18)	0.0606 (7)
H5A	−0.0550	0.0787	0.5402	0.073*
C3	−0.14383 (18)	0.5419 (4)	0.57872 (17)	0.0587 (7)
C2	−0.06444 (16)	0.6353 (4)	0.63143 (16)	0.0533 (6)
H2A	−0.0671	0.7752	0.6553	0.064*
N1	0.18143 (15)	0.5538 (4)	0.72148 (15)	0.0637 (6)
C4	−0.13757 (18)	0.3317 (5)	0.54576 (17)	0.0624 (7)
H4A	−0.1905	0.2642	0.5103	0.075*
C9	−0.23392 (19)	0.6640 (6)	0.5563 (2)	0.0902 (10)
H9A	−0.2224	0.8168	0.5521	0.135*
H9B	−0.2649	0.6388	0.6066	0.135*
H9C	−0.2717	0.6140	0.4960	0.135*
C10	0.32939 (16)	0.7009 (5)	0.71083 (18)	0.0594 (7)
C8	0.25963 (19)	0.6878 (6)	0.7706 (2)	0.0798 (9)
H8A	0.2878	0.6250	0.8330	0.096*
H8B	0.2385	0.8328	0.7809	0.096*
F1	0.51784 (14)	0.7389 (4)	0.54697 (17)	0.1337 (9)
C15	0.38998 (19)	0.5337 (5)	0.7092 (2)	0.0754 (8)
H15A	0.3883	0.4105	0.7464	0.090*
C13	0.45416 (19)	0.7270 (6)	0.5999 (2)	0.0800 (9)
C11	0.33333 (18)	0.8798 (5)	0.6546 (2)	0.0701 (8)
H11A	0.2928	0.9943	0.6544	0.084*
C14	0.45313 (19)	0.5445 (6)	0.6536 (2)	0.0840 (9)
H14A	0.4937	0.4308	0.6529	0.101*
C12	0.3958 (2)	0.8944 (5)	0.5983 (2)	0.0795 (9)
H12A	0.3976	1.0163	0.5604	0.095*

	U11	U22	U33	U12	U13	U23
C1	0.0579 (14)	0.0454 (13)	0.0398 (12)	−0.0019 (11)	0.0216 (10)	0.0035 (10)
O1	0.0752 (12)	0.0557 (11)	0.0887 (13)	0.0113 (9)	0.0373 (10)	−0.0010 (10)
C7	0.0664 (16)	0.0565 (15)	0.0483 (13)	−0.0059 (12)	0.0244 (12)	−0.0014 (12)
C6	0.0675 (16)	0.0451 (14)	0.0507 (13)	0.0023 (12)	0.0312 (12)	0.0029 (11)
C5	0.0812 (18)	0.0508 (15)	0.0591 (15)	−0.0124 (14)	0.0347 (14)	−0.0112 (13)
C3	0.0670 (16)	0.0643 (17)	0.0475 (13)	0.0028 (13)	0.0191 (12)	0.0075 (13)
C2	0.0694 (16)	0.0446 (13)	0.0497 (13)	0.0042 (12)	0.0219 (12)	0.0033 (11)
N1	0.0596 (13)	0.0755 (15)	0.0597 (13)	−0.0104 (12)	0.0216 (11)	−0.0014 (11)
C4	0.0697 (17)	0.0713 (18)	0.0494 (14)	−0.0164 (14)	0.0207 (13)	−0.0049 (14)
C9	0.0684 (19)	0.105 (3)	0.092 (2)	0.0169 (17)	0.0095 (17)	0.018 (2)
C10	0.0463 (14)	0.0720 (18)	0.0561 (15)	−0.0083 (13)	0.0050 (11)	−0.0012 (14)
C8	0.0684 (18)	0.110 (2)	0.0631 (17)	−0.0216 (17)	0.0198 (14)	−0.0138 (17)
F1	0.1096 (15)	0.160 (2)	0.159 (2)	−0.0252 (14)	0.0876 (15)	−0.0185 (16)
C15	0.0673 (18)	0.074 (2)	0.0802 (19)	−0.0018 (15)	0.0096 (15)	0.0124 (16)
C13	0.0612 (18)	0.097 (3)	0.089 (2)	−0.0158 (17)	0.0329 (16)	−0.009 (2)
C11	0.0580 (16)	0.0698 (19)	0.0807 (19)	0.0033 (14)	0.0136 (14)	−0.0013 (16)
C14	0.0587 (17)	0.083 (2)	0.109 (3)	0.0091 (16)	0.0190 (17)	−0.012 (2)
C12	0.078 (2)	0.075 (2)	0.087 (2)	−0.0110 (17)	0.0240 (17)	0.0117 (17)

C1—C2	1.402 (3)	C9—H9B	0.9600
C1—C6	1.409 (3)	C9—H9C	0.9600
C1—C7	1.447 (3)	C10—C11	1.373 (4)
O1—C6	1.352 (3)	C10—C15	1.378 (3)
O1—H1	0.8200	C10—C8	1.508 (3)
C7—N1	1.280 (3)	C8—H8A	0.9700
C7—H7A	0.9300	C8—H8B	0.9700
C6—C5	1.385 (3)	F1—C13	1.360 (3)
C5—C4	1.371 (4)	C15—C14	1.381 (4)
C5—H5A	0.9300	C15—H15A	0.9300
C3—C2	1.372 (3)	C13—C12	1.349 (4)
C3—C4	1.387 (4)	C13—C14	1.362 (4)
C3—C9	1.513 (4)	C11—C12	1.381 (4)
C2—H2A	0.9300	C11—H11A	0.9300
N1—C8	1.466 (3)	C14—H14A	0.9300
C4—H4A	0.9300	C12—H12A	0.9300
C9—H9A	0.9600
C2—C1—C6	118.4 (2)	H9A—C9—H9C	109.5
C2—C1—C7	119.4 (2)	H9B—C9—H9C	109.5
C6—C1—C7	122.2 (2)	C11—C10—C15	117.7 (3)
C6—O1—H1	109.5	C11—C10—C8	120.7 (3)
N1—C7—C1	122.1 (2)	C15—C10—C8	121.6 (3)
N1—C7—H7A	118.9	N1—C8—C10	110.2 (2)
C1—C7—H7A	118.9	N1—C8—H8A	109.6
O1—C6—C5	119.7 (2)	C10—C8—H8A	109.6
O1—C6—C1	121.3 (2)	N1—C8—H8B	109.6
C5—C6—C1	119.1 (2)	C10—C8—H8B	109.6
C4—C5—C6	120.3 (2)	H8A—C8—H8B	108.1
C4—C5—H5A	119.9	C10—C15—C14	121.6 (3)
C6—C5—H5A	119.9	C10—C15—H15A	119.2
C2—C3—C4	117.1 (2)	C14—C15—H15A	119.2
C2—C3—C9	121.4 (3)	C12—C13—F1	119.6 (3)
C4—C3—C9	121.5 (3)	C12—C13—C14	122.7 (3)
C3—C2—C1	122.7 (2)	F1—C13—C14	117.7 (3)
C3—C2—H2A	118.7	C10—C11—C12	121.8 (3)
C1—C2—H2A	118.7	C10—C11—H11A	119.1
C7—N1—C8	117.3 (3)	C12—C11—H11A	119.1
C5—C4—C3	122.5 (2)	C13—C14—C15	118.0 (3)
C5—C4—H4A	118.8	C13—C14—H14A	121.0
C3—C4—H4A	118.8	C15—C14—H14A	121.0
C3—C9—H9A	109.5	C13—C12—C11	118.2 (3)
C3—C9—H9B	109.5	C13—C12—H12A	120.9
H9A—C9—H9B	109.5	C11—C12—H12A	120.9
C3—C9—H9C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.90	2.628 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.90	2.628 (3)	147